1-Indanone, 6-bromo- → 6-Bromo-1-ethylidene-indan

(Ethyl)triphenylphosphonium bromide (14.5 g, 39.1 mmol) was dissolved in 75 mL of tetrahydrofuran followed by addition of potassium tert-butoxide (5.29 g, 47.3 mmol) at room temperature. Upon completion of the addition, the reaction mixture was stirred for 1 hour. A solution of 6-bromo-indan-1-one 38b (3.39 g, 18.6 mmol) in 25 mL of tetrahydrofuran was added to above mixture and the mixture was stirred for another 1 hour. The reaction was monitored by TLC until the disappearance of the starting materials. The reaction was quenched with 150 mL of water and then the mixture was extracted with dichloromethane (50 mL×4). The combined organic extracts were washed with saturated brine (45 mL×2), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 6-bromo-1-ethylidene-indan 41a (3.07 g, 74%) as a yellow oil.

1. additionUpon completion of the addition
2. stirringthe mixture was stirred for another 1 hour
3. customThe reaction was quenched with 150 mL of water
4. extractionthe mixture was extracted with dichloromethane (50 mL×4)
5. washThe combined organic extracts were washed with saturated brine (45 mL×2)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. customto remove the drying agent
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography

ORD record

ord-5537c0a066294379952ba6463770d756

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367710B2